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Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods

a technology of cytoprotective compounds and compounds, applied in the field of cytoprotective compounds, can solve the problems of not always being able to distinguish between "preventing" and "suppressing", exposure to sunlight can pose a number of skin health hazards, and the erythema is a long-term hazard of prolonged exposure to sunligh

Inactive Publication Date: 2003-04-17
JOHNSON & JOHNSON CONSUMER COPANIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It will be understood by those skilled in the art that in human medicine, it is not always possible to distinguish between "preventing" and "suppressing" since the ultimate inductive event or events may be unknown, latent, or the patient is not ascertained until well after the occurrence of the event or events.
For example, exposure to sunlight can pose a number of hazards to the skin.
The major short-term hazard of prolonged exposure to sunlight is erythema, i.e., sunburn, which primarily results from UVB radiation having a wavelength of from about 290 nm to about 320 nm.
Over the long term, however, such prolonged exposure can often cause malignant changes in the skin surface to occur.
Another long-term hazard of ultraviolet radiation is premature aging of the skin, which is primarily caused by UVA radiation having a wavelength of from about 320 nm to about 400 nm.
Although the anatomical degradation of the skin is most advanced in the elderly, the destructive effects of excessive sun exposure are already evident by the second decade.

Method used

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  • Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods
  • Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods
  • Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of 4-[2-(3,4-bis-methoxymethoxy-phenyl)-vinyl]-benzoic Acid Ethyl Ester

[1028] 19

[1029] 1A. (4-Methoxycarbonyl-benzyl)-triphenyl-phosphonium bromide. A solution of, methyl 4-(bromomethyl)-benzoate (2.29 g, 10 mmol) and triphenylphosphine (2.62 g, 10 mmol) in toluene (40 mL) was refluxed for 2 hours and then cooled down to room temperature. The precipitate was filtered and dried under vacuum, giving 4.71 g (95%) of white solid. 20

[1030] 1B. 3,4-Bis-methoxymethoxy-benzaldehyde. To a solution of 3,4-dihydroxbenzaldehyde (2.76 g, 20 mmol, Adrich) in anhydrous N,N-dimethylformamide (DMF, 50 mL, Adrich) was added sodium hydride (1.76 g, 44 mmol, 2.2 eq, 60% in mineral oil, Adrich) portionwise under nitrogen at 0.degree. C. The reaction mixture was stirred at room temperature for 30 min. To the dark blue mixture was added chloromethyl methylether (6.1 mL, 6.44 g, 80 mmol, 4.0 eq, tech, Adrich) dropwise with an ice-water bath and anhydrous potassium carbonate (8.29 g, 60 mmol, 3....

example 2

Preparation of 4-[2-(3,4-Dihydroxy-phenyl)-vinyl]-benzoic Acid Ethyl Ester

[1062] 21

[1063] 2A. To a solution of 4-[2-(3,4-bis-methoxymethoxy-phenyl)-vinyl]-be-nzoic acid ethyl ester (1.0 mmol) of 3 in MeOH (100 mL) at room temperature was added slowly 15 drops of a concentrated HCl solution. The resulting solution was stirred for 12 h. The solvent was then evaporated under reduced pressure and the residue was chromatographed (hexane: EtOAc=1:1) to afford the product as a yellow solid (yield 90%). NMR indicated the purified product contains cis / trans isomers and both ethyl and methyl esters. .sup.1H-NMR (300 MHz, CD.sub.3OD) .delta. 7.98 (d, J=8.4 Hz, 1.82H), 7.87(d, J=8.4 Hz, 0.18H), 7.54 (d, J=8.4 Hz, 1.82H), 7.37 (d, J=8.4 Hz, 0.18H), 7.16-6.92 (m, 4H), 6.81 (m, 1H), 4.41-4.35 (m, 1.9H), 3.92 (m, 0.5H), 1.41 (m, 2.8H).

[1064] 2B. Other Compounds of Formula I Similarly, by following the procedures of Example 2A, there are obtained:

[1065] 4-[2-(3,4-Bis-{2-[2-(2-methoxy-ethoxy)-ethoxy]...

example 3

Preparation of 4-[2-(3,4-Dimethoxymethoxy-phenyl)-vinyl]-nitrobenzene

[1070] 22

[1071] 3A. To a solution of (4-nitrobenzyl)-triphenyl-phosphonium bromide (725 mg, 1.51 mmol, prepared in 97% yield in a similar way as described in Example 1) and 3,4-bis-methoxymethoxy-benzaldehyde (299 mg, 1.38 mmol) in ethanol (20 mL) was added lithium ethoxide (1.45 mL, 1.45 mmol, 1 M in tetrahydrofuran) at room temperature over 4 hours. The resulting solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residues were chromatographed (silica gel, methylene chloride), affording an orange-red product (214 mg, 41%). .sup.1H-NMR (300 Hz, D.sub.3CCl) .delta. (ppm) 8.25-8.05 (m, 2H), 7.65-6.95 (m, 5H), 6.85-6.50 (m, 2H), 5.31 (s, CH.sub.2, 40%), 5.28 (s, CH.sub.2, 40%), 5.23 (s, CH.sub.2, 60%), 5.05 (s, CH2, 60%), 3.56 (s, CH.sub.3, 40%), 3.53 (s, CH.sub.3, 40%), 3.51 (s, CH.sub.3, 60%), 3.38 (s, CH.sub.3, 60%).

[1072] B. Other Compounds of Formula I Simil...

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Abstract

Cytoprotective compounds, many of which are phenolic derivatives characterized by a substituted phenol having certain conjugated bonds, are useful in the treatment of certain ischemic or inflammatory conditions, including but not limited to stroke, myocardial infarction, congestive heart failure, and skin disorders characterized by inflammation or oxidative damage. They are also useful in the manufacture of pharmaceutical and cosmetic formulations for the treatment of such conditions.

Description

[0001] This application claims priority of co-pending provisional applications U.S. Serial No. 60 / 307,439, filed Jul. 23, 2001, and U.S. Serial No. 60 / 353,702, filed Jan. 31, 2002, incorporated herein by reference.[0002] The present invention relates to certain compounds having cytoprotective activity, and particularly to a series of phenolic derivatives. The invention is also directed to formulations and methods for treating stroke, myocardial infarction and chronic heart failure, as well as other oxidative stress-related conditions that are typically responsive to cellular enzyme modulation.BACKGROUND INFORMATION[0003] The present invention is concerned with cytoprotective compounds, many of which are phenolic derivatives characterized by a substituted phenol having certain conjugated bonds, also referred to herein as a "conjugated phenol."[0004] Compositions of the invention are active in certain experimental models that predict efficacy in, for example, certain ischemic or infla...

Claims

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Application Information

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IPC IPC(8): A61K8/00A61K8/30A61K31/05A61K31/055A61K31/06A61K31/085A61K31/09C07D295/18A61K31/10A61K31/122A61K31/15A61K31/166A61K31/18A61K31/192A61K31/21A61K31/235A61K31/277A61K31/28A61K31/30A61K31/315A61K31/343A61K31/353A61K31/36A61K31/381A61K31/4164A61K31/4184A61K31/426A61K31/4425A61K31/444A61K31/4453A61K31/5375A61K31/555A61K31/662A61K31/7024A61K33/32A61P1/04A61P3/10A61P5/24A61P9/00A61P9/04A61P9/10A61P11/00A61P11/06A61P13/12A61P15/00A61P17/00A61P17/02A61P17/06A61P17/10A61P17/16A61P19/02A61P21/00A61P25/00A61P25/02A61P25/16A61P25/18A61P25/28A61P27/02A61P29/00A61P37/06A61P43/00A61Q19/00A61Q19/02C07C39/21C07C39/373C07C39/44C07C43/215C07C43/23C07C45/30C07C45/71C07C49/737C07C49/747C07C50/34C07C69/007C07C69/76C07C69/94C07C205/17C07C205/20C07C205/22C07C205/35C07C205/57C07C235/42C07C255/15C07C255/36C07C255/53C07C255/54C07C311/29C07C317/22C07D213/30C07D213/53C07D231/22C07D231/26C07D233/24C07D233/64C07D235/08C07D277/20C07D277/24C07D277/30C07D277/34C07D295/22C07D295/26C07D307/83C07D311/72C07D317/62C07D333/16C07F1/08C07F9/40C07H13/08
CPCC07C43/23C07C45/30C07F9/4021C07D311/72C07D295/26C07C45/71C07C49/737C07C69/94C07C205/17C07C205/20C07C205/22C07C205/35C07C205/57C07C235/42C07C255/36C07C311/29C07C2103/24C07D213/30C07D213/53C07D231/26C07D277/20C07D277/24C07C47/575C07C2603/24A61P1/04A61P11/00A61P11/06A61P13/12A61P15/00A61P17/00A61P17/02A61P17/06A61P17/10A61P17/16A61P19/02A61P21/00A61P25/00A61P25/02A61P25/16A61P25/18A61P25/28A61P27/02A61P29/00A61P37/00A61P37/06A61P43/00A61P5/24A61P9/00A61P9/04A61P9/10A61P3/10
Inventor WANG, BINGZHANG, YONG-KANGCHEN, JIANZHANG, WEISONG, JIANGAODEL BALZO, UGHETTABROWN, LESLEYBODDUPALLI, SEKHARBOBZIN, STEVENGILAT, SYLVAINMILLER, GUY
Owner JOHNSON & JOHNSON CONSUMER COPANIES
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